Journal article
Direct Conversion of Nitriles into Alkene “Isonitriles”
Angewandte Chemie (International ed.), v 55(47), pp 14770-14773
14 Nov 2016
PMID: 27778438
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
The sequenced addition of RLi to nitriles, trapping with isopropylformate, and dehydration with phosphoryl chloride provides an efficient, direct synthesis of alkene isocyanides. The one‐pot sequence involves a series of carefully orchestrated steps: addition, formylation, tautomerization, and dehydration, with CuCN catalyzing a key equilibration of a formyl imine to an N‐formyl enamine. The resulting aromatic alkeneisocyanides, that are otherwise challenging to synthesize, engage in an unusual [4+2]‐type cycloaddition/1,3‐H shift/decyanation sequence to afford substituted naphthalenes.
An orchestrated sequence: An efficient synthesis of alkeneisocyanides is achieved through the sequenced addition of RLi to nitriles, formylation, and dehydration. A key step in this one‐pot sequence is a CuCN‐catalyzed equilibration of a formyl imine to an N‐formyl enamine. The utility of the reaction is illustrated in a new [4+2]‐type cycloaddition/1,3‐H shift/decyanation.
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Details
- Title
- Direct Conversion of Nitriles into Alkene “Isonitriles”
- Creators
- Yajun Li - Drexel UniversityFraser F. Fleming - Drexel University
- Publication Details
- Angewandte Chemie (International ed.), v 55(47), pp 14770-14773
- Publisher
- Wiley
- Number of pages
- 4
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000388252700051
- Scopus ID
- 2-s2.0-84995687003
- Other Identifier
- 991019169647404721
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InCites Highlights
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- Web of Science research areas
- Chemistry, Multidisciplinary